(+)-(2R,3R)-3-benzyloxy-1,2-epoxyoctane | 102389-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(2R,3R)-3-benzyloxy-1,2-epoxyoctane
• 英文别名: (2R)-2-[(1R)-1-phenylmethoxyhexyl]oxirane
• CAS: 102389-99-1
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: NUTCWDLHCHFJNS-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(2R,3R)-3-benzyloxy-1,2-epoxyoctane 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 18.25h， 生成 (-)-(4R,5R)-5-benzyloxydec-1-yn-4-ol
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Petromyroxol, Enabled by Rhodium-Catalyzed Denitrogenation and Rearrangement of a 1-Sulfonyl-1,2,3-Triazole

  摘要：

  Petromyroxol is a nonracemic mixture of enantiomeric oxylipids isolated from water conditioned with larval sea lamprey. The (+)-antipode exhibits interesting biological properties, but only 1 mg was isolated from >100 000 L of water. Recently, transition-metal-catalyzed denitrogenation of 1-sulfonyl-1,2,3-triazoles has emerged as a powerful strategy for the synthesis of value-added products, including efficient diastereocontrolled construction of tetrahydrofurans. This methodology enabled the rapid development of the first synthesis of (+)-petromyroxol in 9 steps and 20% overall yield from a readily accessible starting material.

  DOI：

  10.1021/acs.joc.5b00399
• 作为产物：
  描述：

  (E)-1-chlorooct-2-ene 在 四氧化锇 、 甲基磺酰胺 、 水 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 37.0h， 生成 (+)-(2R,3R)-3-benzyloxy-1,2-epoxyoctane
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Petromyroxol, Enabled by Rhodium-Catalyzed Denitrogenation and Rearrangement of a 1-Sulfonyl-1,2,3-Triazole

  摘要：

  Petromyroxol is a nonracemic mixture of enantiomeric oxylipids isolated from water conditioned with larval sea lamprey. The (+)-antipode exhibits interesting biological properties, but only 1 mg was isolated from >100 000 L of water. Recently, transition-metal-catalyzed denitrogenation of 1-sulfonyl-1,2,3-triazoles has emerged as a powerful strategy for the synthesis of value-added products, including efficient diastereocontrolled construction of tetrahydrofurans. This methodology enabled the rapid development of the first synthesis of (+)-petromyroxol in 9 steps and 20% overall yield from a readily accessible starting material.

  DOI：

  10.1021/acs.joc.5b00399

文献信息

• Synthesis of the rarely obtained syn-adducts in the reaction of organocopper compounds with 2,3-O-isopropylideneglyceraldehyde. Preparation of optically active epoxy alcohols
  作者：Fumie Sato、Yuichi Kobayashi、Osamu Takahashi、Tsunehisa Chiba、Yoshiyuki Takeda、Masato Kusakabe

  DOI：10.1039/c39850001636

  日期：——

  Organocopper compounds, prepared from Grignard reagents and copper(I) iodide in tetrahydrofuran-dimethyl sulphide, react with 2,3-O-isopropylideneglyceraldehyde highly stereoselectively (>10:1) affording the rarely obtained syn-addition products which can be readily converted into optically active epoxy alcohols, useful intermediates in organic synthesis.

  由格氏试剂和碘化亚铜（I）在四氢呋喃-二甲基硫醚中制备的有机铜化合物与2,3- O-异亚丙基甘油醛高度立体选择性（> 10：1）反应，提供了很少获得的合成加成产物，可以轻松地将其转化为旋光性环氧醇，在有机合成中有用的中间体。
• SATO, FUMIE;KOBAYASHI, YUICHI;TAKAHASHI, OSAMU;CHIBA, TSUNEHISA;TAKEDA, Y+, J. CHEM. SOC. CHEM. COMMUN., 1985, N 22, 1636-1638
  作者：SATO, FUMIE、KOBAYASHI, YUICHI、TAKAHASHI, OSAMU、CHIBA, TSUNEHISA、TAKEDA, Y+

  DOI：——

  日期：——